On the morning of November 15th, 2017, twenty-four-year-old Sydney Loofe finished her shift as a cashier at Menards in Lincoln, Nebraska. She uploaded a picture to her social media with the caption “ready for my date”. The next day, Sydney failed to show up for her shift at Menards. It was very unlike Sydney to not show up to work, so her friends and family were immediately concerned. The missing persons case began, with family alerting investigators that Sydney had been on a date the night before with a woman named “Audrey” that she met on Tinder.
Sydney Irene Loofe was born on August 21st, 1993, in Broken Bow, Nebraska. Her parents, George and Susie, moved to Neligh, Nebraska in 2000. George became a high school principal while Susie worked as a resource teacher at Neligh-Oakdale High School. Sydney was the middle child, with a brother and sister. She graduated from Neligh-Oakdale High School in 2011 where she was a member of the band and played golf and basketball. Sydney was also an avid fisherman. Following her graduation, Sydney agreed to a transfer for work and moved into her own apartment in Lincoln, Nebraska.
Sydney was an independent young woman, but she was not without troubles. Sydney had struggled with anxiety and depression. Her family told authorities in the days before her disappearance, Syndey had told her family about worsening mental health. In fact, her family had driven her to a doctor’s appointment where she was prescribed anti-depressants. Initially, detectives had to consider the missing girl may have disappeared on purpose or harmed herself.
Despite the possibility that Sydney had hurt herself, there were signs that something more sinister had occurred. Police performed a welfare check at her apartment at her mother’s request. Sydney was not present, but her cat was there and unfed. Her purse, glasses, and car were also left at the home. The possibility that she disappeared on her own was looking less likely. Her cell phone last pinged in Wilber, Nebraska at 8:32 pm on November 15th, 2017.
Friends of Sydney knew that she had been on a date the night she was last seen. On November 14th, Sydney had gone on her first date with “Audrey” from Tinder. Records showed she asked Audrey twice if it was just going to the two of them, which Audrey confirmed. On November 15th, Sydney planned to go on another date with the girl she met on Tinder. Her friends found the profile for Audrey on Tinder and let the police know the identity of the date Sydney had. The girl was actually Bailey Boswell.
Bailey Marie Boswell was born February 26th, 1994, in Iowa. Her father was murdered when she was just a toddler, but she was later adopted by her stepfather. Bailey enjoyed a relatively stable and supportive childhood in Iowa. She was a standout athlete, excelling in basketball. When Bailey was in college, she started dating a man who allegedly sexually and physically abused her. He eventually started forcing her into illegal activities such as prostitution. Bailey’s mother said her daughter started abusing drugs and alcohol before dropping out of college. At one point, she was treated for alcohol poisoning.
After she dropped out of college, Bailey became pregnant by her abusive boyfriend. He continued to physically abuse her throughout her pregnancy. Bailey gave birth to a daughter sometime in 2016, but the baby was removed from her care due to abuse from her boyfriend and drug abuse in the home. Bailey’s mother gained full custody of the child. Eventually, Bailey ended the relationship and moved back in with her parents.
The reunion was short-lived, however. Bailey’s mother said that she was not the same girl as before her abusive relationship. She lacked self-esteem. In the summer of 2016, Bailey met Aubrey Trail and soon moved to Wilber, Nebraska to live with the man. Aubrey Clifton Trail was born September 7th, 1966. He was fifty years old when he started dating the twenty-two-year-old Bailey Boswell.
Aubrey Trail had a tumultuous life. He was abused and neglected before being abandoned by his parents at the age of two. His grandparents then began caring for him, but it seems they lacked respect for the law. Trail’s mother later married his stepfather, who adopted the boy. Trail’s stepfather and mother were abusive and neglectful throughout his childhood. By the time he was a teenager, Aubrey was in a juvenile detention center. At age seventeen, he went to prison for the first time for armed robbery. Aubrey Trail would spend most of his adult life either in prison or on parole for various offenses.
When investigators pinned down Syndey Loofe’s last phone ping to the duplex in Wilbur where Aubrey Trail was living with Bailey Boswell, they performed a welfare check hoping that the young woman was safely in the home. There was no answer, but the landlord granted the police access to the home. Nothing seemed out of the ordinary or alarming, except a pungent smell of bleach. The bleach smell was so bad that a member of the family in the adjacent duplex got sick to her stomach and developed hives from the stench of bleach. A search warrant was obtained for the home, but nothing significant was found inside.
Thanksgiving came and went, with no signs of Sydney. Her family’s holiday was marred by the devastation of Sydney not being present. Meanwhile, Aubrey Trail and Bailey Boswell were considered persons of interest in the case. However, they never returned to their home. They appeared to be on the run. They were also wanted for an unrelated crime. The couple were accused of scamming a couple out of $400,000 under the pretense of using the money to sell a lucrative gold coin, creating a profit for both parties. Trail allegedly told the couple he would kill them if they didn’t cooperate, and the couple gave them money to fly to Paris where Trail was supposed to meet the coin dealer. The indictment for this crime goes on to say that Bailey Boswell bought a gun and told a friend they planned to kill a coin dealer.
On November 28th, 2017, Bailey Boswell and Aubrey Trail posted a video to social media in which they discuss their involvement with Syndey Loofe and address speculation that they were involved in her disappearance. Aubrey talks first, explaining that he and Bailey do not know Syndey’s whereabouts and hope that she is found safely. Bailey, who appears to be disguising herself with a hat and sunglasses, explains that she went on a date with Sydney. She claims on the night of November 15th she picked Sydney up and the two girls drove around smoking weed. She said that Sydney then asked to be dropped off at a friend’s house, which Bailey said she did. Bailey explains that she did use an alias on Tinder, “Audrey”, because she has warrants out for her arrest. Both denied being involved in Sydney’s disappearance.
On November 30th, Aubrey and Bailey were arrested in Branson, Missouri, on fraud charges and taken into custody. The couple were in possession of maps, sleeping bags, and hiking shoes. It is believed the couple were planning to flee to Mexico. Under interrogation, Aubrey Trail appeared arrogant. He stated that he did not know where Syndey was and that Bailey “would never tell them anything”. He tried to exert control over the conversation and appeared to be playing games with investigators.
The detectives were relatively sure that Aubrey Trail and Bailey Boswell were responsible for Sydney’s disappearance. They used electronic data from the cell phones of the suspects and victim as “breadcrumbs”. On December 4th, 2017, police found an arm with Syndey’s tattoo on it in a ditch along the path Trail and Boswell took on December 16th. The arm was identified as belonging to Syndey by her tattoo, which read “Everything will be wonderful someday”. Over the next two days, thirteen of fourteen pieces of Sydney Loofe’s body. One of her upper arms and most of her internal organs were never found. Months later, Syndey’s bra and the shirt she was wearing November 15th were found.
The autopsy on Syndey Loofe’s remains determined that the young woman had been strangled to death. Her hyoid bone was broken and petechiae were noted around her eyes, indicative of strangulation. Her body was then cut into fourteen pieces and placed in trash bags. She had signs of blunt force trauma on her head and bruises on her back and thigh. Syndey’s earring had been torn from her ear. There were several superficial lacerations to her body as well. Her wrists showed ligature marks indicative of her being restrained. The pathologist believed the mutilation of her body was caused by a sharp instrument and was not related to animals after disposal.
Aubrey Trail, in custody on the fraud charges, gave numerous confessions to Syndey’s murder after the remains were found. He told investigators that he drank her blood, explaining the numerous superficial lacerations. In some of his confessions, Aubrey Trail incriminates Bailey Boswell as a participant. In others, he denies that she was ever a part of the crime. In one confession, Trail claimed that Syndey had agreed to participate in a sexual fantasy involving erotic asphyxiation. He said she was killed accidently during the encounter. Although he told numerous stories about how Syndey died, Aubrey led police to a cemetery where he dumped her personal belongings. Here, they found her phone, driver’s license, and credit card.
Aubrey Trail and Bailey Boswell were charged with first-degree murder, conspiracy to commit murder, and improper disposal of human remains. The State of Nebraska announced they were seeking the death penalty against both defendants. If give a death sentence, Bailey Boswell would be the only woman on Nebraska’s death row. In fact, Nebraska did not even have a death row set up for female inmates. Bailey would either have to be housed in general population or would suffer severe isolation with no other women on death row in the state.
At trial, clerks at a local hotel testified that they had seen Aubrey Trail, Bailey Boswell, and Syndey Loofe at the hotel weeks before the murder occurred. Surveillance footage also showed Trail and Boswell checking into a hotel near Menards, where Loofe worked, on November 14th. The morning of November 15th, Boswell and Trail went shopping at a local antique mall and purchased a folding saw, a weeder, and food grinders. Cell phone data shows that following their purchase, Trail and Boswell followed Loofe from her apartment to Menards. On surveillance, Trail is seen entering the Menard’s store as Loofe exited, looking over his shoulder at her as she passed.
Further surveillance footage shows that Trail and Boswell purchased a hacksaw, wire snips, drop clothes, a knife, and replacement blades from a local Home Depot before the murder. At Menards, Trail purchased air fresheners, cotton cord, lighters, protein bars, and a thermometer. A few hours before the murder occurred, Bailey and Aubrey purchased plastic bags consistent with those in which Syndey’s body was found and a few gallons of bleach from a local Dollar General. A clerk testified that on November 16th, the day after the murder, Bailey Boswell bought more bleach, Drano, more plastic bags, and a trash bin.
Cell phone data was presented that showed Boswell leaving the store on November 16th and traveling to the location where Syndey’s body was found. The hacksaw and cord were not found, but detectives did present other evidence they found during the investigation. Handcuffs, ropes, a dog collar, a leash, and sex toys were found on subsequent searches of Trail and Boswell’s home. The defense pointed out that Loofe’s DNA was not found on any of these items. Electric wire found near the body parts was identified as the murder weapon by Aubrey Trail, but no DNA or fingerprints were able to conclusively prove Trail or Boswell had handled the items.
Three women testified that they had each been involved in a sexual relationship with Trail and Boswell between July and November of 2017. The first said that she had met Boswell through a dating app with Boswell utilizing an alias. She said that Trail claimed to be a vampire and that he had twelve girls that were his witches. Trail told her that Bailey Boswell was the “head witch”. Trail urged the girl to join their group, similar to a cult by description, to get revenge on her stepfather. In interviews with detectives, Trail admitted to targeting young girls with substance abuse and family issues as they made good targets.
The woman went on to testify that Trail told her they planned to kill someone and invited her to help. She said she became sexually involved with Trail and Boswell, describing the encounters as involving erotic asphyxiation. She described rules she was made to follow including checking in with Bowell and Trail every three hours when not with them, being naked at all times when in the apartment, and having to ask permission for everything including using the bathroom. If she misbehaved, she claimed she was physically abused.
This witness testified that Bailey Boswell, using an alias, would connect with young women and then pass the phone to Aubrey Trail. Trail would communicate with the women as “Audrey” via text, giving the phone to Bailey only when phone calls were required. The woman claimed that Aubrey Trail asked her if she wanted the lady he was talking with to be her first kill. She testified that another girl who was part of the “coven” was also targeted as a murder victim at one point by Trail, at which time she terminated her relationship with the pair.
The second woman testified that she had also met the couple through a dating app in which Boswell used an alias. Her testimony corroborated much of the first woman’s testimony, and also included that Aubrey Trail told her he planned to kill and torture a woman on video tape and sell the tapes for money. He claimed that he and Boswell would be rich after selling the tapes. She said she left the group when Trail became more insistent that she torture and kill someone.
The third woman testified that she met the couple just a month before the murder. She said that Bailey Boswell told her that she and Trail were in a dominate and submissive relationship and that Trail was part of the deal if she wanted to be in a relationship with Boswell. She claimed that Boswell and Trail talked about being witches and committing violent crimes against women. This witness said she had a severe asthma attack on November 15th, 2017, and went to her family’s home in Omaha.
This woman stated that Bailey told her on November 15th that she and Trail would be busy the next few days. She saw the couple again on November 17th, stating that the couple seemed quieter. Trail allegedly told her they were going to kill someone and threatened her until she agreed to participate. Trail then told her not to worry about it because she had already proven her loyalty to him by agreement. Over the next several days, the third witness said that she drove the couple all over Nebraska while they discussed finding someone to kill and torture for money. The witness finally returned home by herself when her mother filed a missing persons report on her.
Aubrey Trail took the stand in his own defense, stating that most of the prosecution’s case was undisputed by him. He agreed that he and Bailey discussed torturing and killing frequently, but claimed they were only fantasies for the couple. He admitted to speaking of witchcraft and reincarnation often. He claimed he met Syndey Loofe in the Spring of 2017 and she helped he and Boswell in their antique selling schemes. He said Loofe wanted out of the arrangement in September of 2017. According to Trail, Boswell used an alias to lure Syndey out on another date and Syndey was upset by this when she realized it was actually Boswell and Trail.
Trail claimed the items purchased in the days before the murder were for cleaning antiques and not premeditation of murder. He said Loofe came to their home on November 15th with plans to rejoin the coven. Trail claimed that Syndey agreed to participate in erotic asphyxiation during sex with him, during which he accidentally killed her. He said he did not call 911 because he has a lengthy criminal history and was in possession of drugs and stolen goods at the time.
On the third day of Aubrey Trail’s trial, Trail suddenly shouted “Bailey is innocent, and I curse you all” before slitting his own throat with a razor blade that he smuggled into the courtroom. His wounds were superficial and only required minor medical attention. The prosecution believes this was an attempt to derail the trial and just another act of manipulation on the part of a psychopath. The defense requested a mistrial, which was denied.
Aubrey Trail was convicted of first-degree murder, conspiracy to commit murder, and improper disposal of a human corpse. The state sought the death penalty. The penalty phase was presided over by a three-panel judge. Aggravating circumstances included apparent relishing of the murder by the killer, senselessness of the crime, helplessness of the victim, infliction of gratuitous violence to the victim, and senseless dismemberment of the body. The defense’s only mitigating factor was the claim that the victim willingly participated in the deviant sexual behavior that allegedly led to her death. Aubrey Trail was sentenced to death.
Bailey Boswell went to trial after her co-conspirator. The same evidence was presented against Bailey, and she was also found guilty on all three charges. By this time, it was 2021 and four years after the murder. Bailey’s parents begged the three-panel judge not to sentence her to death for the sake of her then five-year-old daughter. The panel had to anonymously agree that the State of Nebraska proved the crime was particularly depraved. One judge dissented, so Bailey Boswell was sentenced to life in prison without parole.
Bailey Boswell is currently serving a life sentence at the Nebraska Correctional Center for Women. Aubrey Trail is on death row at the Tecumseh State Correctional Institution. Both have appealed their convictions and sentences, but all appeals have so far been denied. In 2023, Aubrey Trail waived all further appeals and asked the State of Nebraska to set an execution date. He claims that accepting his sentence is the only way he can apologize to Sydney’s family, but others believe this is yet another attempt for him to exert control.
The State of Nebraska has not carried out an execution since 2018 due to the lack of availability of lethal injection medications. There are currently eleven men on Nebraska’s death row including John Lotter, the man who murdered Brandon Tina and two others in 1993 because Tina was transgender. It is unclear when Nebraska will resume executions.
References
Signs of a Psychopath (2023) “This is What I Chose to Be”- Available on Discovery+
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